Apart from what I have learned about entrepreneurialism from my interactions with some of the country’s most brilliant minds, I have soaked up some wisdom about the meaning of life. Here are my top ten favourite insights, culled from twelve years in the charitable sector:

1. “To whom much is given, much is expected.” Bill Gates, quoting his late mother, shared these words in a 2007 address to the graduating class of Harvard University. It’s something all philanthropists have told me. If you are healthy, educated and never wanted for food or shelter, you owe it to the majority of the world to pay it forward.

2. Believe in your own greatness. I have worked with philanthropists who lost their entire families in the Holocaust. Philanthropists have taught me that even if you were born into harrowing circumstances, never doubt your capacity to overcome the odds. You were created to be great.

3. Humility is king. Many philanthropists I know have an uncanny sense of humility. One of the most inspiring was orphaned as a child. Growing up vulnerable has made him more compassionate and humble. It has given him an empathetic edge which sets him apart as a philanthropist and a human being.

4. Money is a means, not an end. Remember Robin Leach’s “champagne wishes and caviar dreams” in Lifestyles of the Rich and Famous? The show reduced wealth to soulless materialism and ostentatious narcissism. One would think that wealth was only about Bentleys, yachts and villas. Philanthropists have taught me that the best part of wealth is giving it away in service to something greater than yourself.

5. Never be the smartest person in the room. I have heard many philanthropists say this. The point is to surround yourself with people who command your “A” game. The subtext? Keep your ego in check. It’s hard to respect, let alone tolerate, a braggart. (Even the word braggart is annoying).

6. Be the first to give credit away. A mark of many great philanthropists is their ability to shine the spotlight on others; whether nonprofit staff, clients or their families. Gratitude is one of the most powerful forces in the world.

7. Root for the underdog. I know several philanthropists who will only fund the projects that no one else will touch. Give me the most stigmatized cause, the most complex client group! What does this teach us about life? The nobility of standing in solidarity with the marginalized. Everyone from Churchill to Dostoyevsky to Gandhi argued that the true measure of a civilization’s greatness is how it treats its most vulnerable members.

8. Stop thinking outside the box. The adage to “think outside the box” always rubbed me the wrong way. Maybe because it’s used so much that I associate it with the antithesis of creativity, the very thing it is supposed to evoke. Instead of thinking outside the box, one philanthropist I know talks a lot about the “box cover,” a metaphor I much prefer. His point is that no matter how complex a problem, if you can visualize the big picture, you can make it happen. People become so distracted by the minutiae of problems that they lose sight of the master plan.

9. Be just, not charitable. The great 12th century teacher Maimonides, also known as RamBam, taught that the highest form of social justice is to empower someone to help themselves, whether it’s by offering them an interest-free loan to start their own business or opening the door for them to find a meaningful job. Philanthropists have taught me that people do not want hand outs. They want to be self-sufficient, empowered, in charge of their destiny. Giving someone a fishing rod, instead of a fish, is a vital lesson about the difference between enabling versus empowering the people in our lives.

10. Generosity makes you rich. I have never heard a philanthropist lament: I wish I didn’t give that money away to feed the hungry! You can never give away too much. The take away here (and you don’t have to be rich to put this into practice) is to be generous with your time, your talent and your treasure, the holy trifecta philanthropist Seymour Schulich references in Get Smarter. One of my favourite experiences working in nonprofit was receiving a $100 donation from a family living in poverty, who had received a hand up to own their own affordable, interest-free home. I photocopied that cheque and looked at it every time I had a low moment at work. Everybody can be a philanthropist.

The ultimate lesson philanthropists have taught me is that no dream or idea, no matter how pie-in-the-sky or crazy it may seem to others, is out of reach. Who would have thought The Giving Pledge would actually work? Today, because of Melinda and Bill Gates’ aspirational dream, the world’s wealthiest people and families are dedicating the majority of their fortunes to philanthropy in their lifetime.

We live in a world where reputations are built on ambition and accomplishments. There’s nothing wrong with “champagne wishes and cavier dreams.” Ambition is commendable, but accomplishments in the service of others, well, they’re sweeter than even the best bubbly money can buy. Just ask any philanthropist.

Kim Smiley is Vice President of Community Capacity Building at UJA Federation of Greater Toronto. She is also the creative force behind Sapphô by Kim Smiley, a social enterprise that promotes beauty for the public good and poetry for the people. You can follow Kim on Twitter, @SapphoByKim

Kim is the recipient of many prestigious academic honours, including the John E. Thayer Award, bestowed by Harvard University to the student who graduates at the top of their class. This article was originally published in the Huffington Post as “Why Philanthropy is the Best Medicine.”